EP0185490B1 - Antibacterial cream - Google Patents
Antibacterial cream Download PDFInfo
- Publication number
- EP0185490B1 EP0185490B1 EP85308814A EP85308814A EP0185490B1 EP 0185490 B1 EP0185490 B1 EP 0185490B1 EP 85308814 A EP85308814 A EP 85308814A EP 85308814 A EP85308814 A EP 85308814A EP 0185490 B1 EP0185490 B1 EP 0185490B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- cream
- topical
- polyol
- base
- hydrocarbon
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Definitions
- This invention relates to topical, antibacterial creams particularly those suitable for topical application to burns, especially those containing the iodophor polyvinylpyrrolidone (povidone) iodine.
- Topical Creams containing antibacterial agents, especially iodophors, are effective therapeutics for the treatment of burns and other skin disorders requiring rectification.
- this therapy is limited by the degree of penetration of the active substance through necrotic tissue, pus and other barriers between the surface of the wound and the deep areas of the wound.
- significant therapeutic advantages are gained by using an additional topical preparation (often acidic in nature) to destroy these barriers and allow free penetration of the antibacterial agent deep into the wound.
- Povidone iodine compositions are known in the art. For example, antiseptic skin ointments are described in US Patent 4,301,145. Reference to other povidone iodine containing compositions is made in the discussion of the background art disclosed therein.
- a topical, antibacterial cream containing an effective quantity of povidone iodine in a topical cream base, wherein the base is an oil-in-water emulsion containing water and 20 to 50 per cent (w/w) of a mixture of at least one hydrocarbon component and at least one polyol moisturising component.
- the present cream has a far greater hydrocarbon/moisturiser content than prior art products.
- the present inventor has surprisingly found that this increased level of hydrocarbon/moisturiser in the cream results in an improved penetration of the antibacterial agent into wound tissue and thereby avoids the need for a preliminary (acidic) treatment and also leads to faster patient recovery.
- Polyvinylpyrrolidone (povidone) is a non-ionic, non-detergent water-soluble, organic polymer that is characterised by an unusual complexing ability, by its colloidal properties and by its physiological inertness. Its iodine complex, polyvinylpyrrolidone (povidone) iodine, is a well known iodophor that is a highly effective germicide, providing a broad spectrum of microbiocidal action against virtually all microbes.
- Povidone iodine may be prepared by any of a number of known routes, see, for example, European Published Applications No. EP-A-120301 and EP-A-6340, and British Patent No. GB-A-1580596.
- the amount of iodine incorporated in the iodophor used in the present cream will be determined by, amongst other factors, the amount of iodophor present in the cream and the required antibacterial strength of the cream.
- iodine will constitute between 1 and 20% (by wt.), especially between 2 and 15% (by wt.) of the iodophor dry weight.
- the concentration of povidone iodine in the present cream will depend on the anti bacterial strength required. In addition, antibacterial agent concentration will be determined by, amongst other factors, the propensity of the agent to cause irritation, the length of use contemplated, the amount of iodine in the iodophor and the rate of iodine loss (when the cream is in use).
- the cream preferably contains enough iodophor to afford a concentration of available (titratable) iodine within the cream of between 0.1 and 2% (by wt.), especially between 0.2 and 1.5% (by wt.).
- a cream employing povidone iodine, with 10% (by wt.) available iodine, as an antibacterial agent would preferably contain between 1 and 20%, especially 2 and 15% (by wt.) of povidone iodine.
- the topical cream base of the present invention is an oil in water emulsion and must contain between 20 and 50 per cent (by wt.) of a mixture of hydrocarbon and polyol moisturising components.
- the cream base contains between 25 and 40 per cent (by wt.) of hydrocarbon/moisturising components.
- the at least one hydrocarbon component of the present, cream base may be selected from any of the hydrocarbon oils and hydrocarbon bases that are well known in the pharmaceutical art. Suitable the hydrocarbon oils are mineral oil or liquid petrolatum, whilst suitable hydrocarbon bases are white petrolatum or white ointment (petrolatum with 5% beeswax).
- the at least one hydrocarbon components comprises between 15 and 40% (w/w), especially between 20-30% (w/w) of the topical cream base.
- the at least one hydrocarbon component comprises a mixture of liquid petrolatum and white petrolatum.
- the at least one polyol moisturising component of the present cream base may be selected from any of the polyol moisturising components that are well known in the pharmaceutical art.
- Examples include propylene glycol and, which is preferred, glycerin.
- the at least one polyol moisturising component comprises between 5 and 20% (w/w), especially between 5 and 15% (w/w) of the topical cream base.
- ratios (w/w) between 1 to 1 and 4 to 1, especially a weight ratio of about 2 to 1, provide the most satisfactory cream bases for incorporation in the present topical cream.
- the present cream base will generally also contain at least one emulsifier, and, optionally but preferably, at least one surfactant.
- Suitable emulsifiers include higher fatty alcohols, such as cetyl alcohol, stearyl alcohol, and cetostearyl alcohol, and partially esterified polyols such as glyceryl monostearate, polyethylene glycol monostearate and sorbitan monooleate.
- emulsifiers are provided at a concentration between 1 and 15% (by wt.) of the cream base.
- the present antibacterial cream must be of a viscosity that allows its topical application to the human or animal body.
- the cream will have a viscosity, at 25°C between 25,000 and 67,000 centipoises, when measured on a Brookfield (Trade Mark) LV Viscometer preferably between 30000 and 50000 centipoises.
- a process for the preparation of a topical, antibacterial cream comprising forming a mixture of an effective quantity of povidone iodine and a topical cream base, wherein the base comprises 20 to 50% (w/w) of a mixture of at least one hydrocarbon component and at least one polyol moisturising component.
- the cream is prepared by forming an aqueous solution containing at least one antibacterial agent and at least one polyol moisturising component and then mixing this aqueous solution with the at least one hydrocarbon component.
- the cream is prepared by forming an aqueous solution of at least one polyol moisturising component, mixing the aqueous polyol solution with at least one hydrocarbon component to form a base and adding an aqueous solution of the antibacterial agent to the base.
- further components e.g. emulsifiers, may be dissolved in either the aqueous or the hydrocarbon phase, as desired.
- the present cream may be administered to the human or animal body by any of the conventional methods known in the medical/pharmaceutical art.
- the cream may first be applied to a suitable dressing, such as a Teflon dressing, which is then placed on the wound tissue.
- the dressing may be held in place by a bondage.
- the dressing will be replaced every 12 to 24 hours.
- the cream may be applied alone or, although this is not necessary for successful treatment, in combination with a known acid cream, for example a benzoic acid containing cream, such as Aserbine (Trade Mark).
- a topical antibacterial cream having the following ingredients was prepared as follows: The stearyl alcohol, cetyl alcohol, white petrolatum, liquid petrolatum, sorbitan monostearate and polyoxyethylene stearate were melted with mixing. Separately, PVPI was dissolved in water, after which the pH of the solution was adjusted to about 4.5 using NaOH.
- the resulting cream had a viscosity of 40000 centipoise at 25°C, measured on a Brookfield LV viscometer.
- a topical, antibacterial cream having the following ingredients was prepared as described in Example 1:
- Topical burn therapy comparing povidone iodine ointment or cream plus aserbine and povidone iodine cream
- the groups were comparable for age, size, type, depth and distribution of burn.
- TAB Trypticase Soy Bean Casein Digest Broth
- TSA Agar
- a stock culture of the test organism was maintained on TSA slants and was transferred to TSB 24 hours prior to the test.
- 0.2 ml. of the TSB culture was added to 5g. of each agent.
- a 4mm loopful of the mixture was removed at intervals and was transferred to 10 ml. of TSB.
- all cultures were examined for growth. Organism viability and carry over controls were carried out and were positive for growth for each agent.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Organic Chemistry (AREA)
- Oncology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Materials For Medical Uses (AREA)
- Dairy Products (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
- This invention relates to topical, antibacterial creams particularly those suitable for topical application to burns, especially those containing the iodophor polyvinylpyrrolidone (povidone) iodine.
- Topical Creams containing antibacterial agents, especially iodophors, are effective therapeutics for the treatment of burns and other skin disorders requiring rectification. However, this therapy is limited by the degree of penetration of the active substance through necrotic tissue, pus and other barriers between the surface of the wound and the deep areas of the wound. In these cases, significant therapeutic advantages are gained by using an additional topical preparation (often acidic in nature) to destroy these barriers and allow free penetration of the antibacterial agent deep into the wound.
- It is a disadvantage of this method of treatment however, that the application of the additional (acidic) preparation must be highly controlled, since it is the intention to remove surface barriers only and not to penetrate this extra medication deep into the wound itself, where further tissue damage could result from acidic attack.
- It is one object of the present invention to provide a topical, antibacterial povidone iodine cream that is suitable for topical application to burns, and that is effective without the use of an acidic preparation, (to destroy surface barriers).
- Other objects and advantages of the present invention will become apparent from the following detailed description thereof.
- Povidone iodine compositions are known in the art. For example, antiseptic skin ointments are described in US Patent 4,301,145. Reference to other povidone iodine containing compositions is made in the discussion of the background art disclosed therein.
- According to the present invention, there is provided a topical, antibacterial cream containing an effective quantity of povidone iodine in a topical cream base, wherein the base is an oil-in-water emulsion containing water and 20 to 50 per cent (w/w) of a mixture of at least one hydrocarbon component and at least one polyol moisturising component.
- The present cream has a far greater hydrocarbon/moisturiser content than prior art products. The present inventor has surprisingly found that this increased level of hydrocarbon/moisturiser in the cream results in an improved penetration of the antibacterial agent into wound tissue and thereby avoids the need for a preliminary (acidic) treatment and also leads to faster patient recovery.
- Polyvinylpyrrolidone (povidone) is a non-ionic, non-detergent water-soluble, organic polymer that is characterised by an unusual complexing ability, by its colloidal properties and by its physiological inertness. Its iodine complex, polyvinylpyrrolidone (povidone) iodine, is a well known iodophor that is a highly effective germicide, providing a broad spectrum of microbiocidal action against virtually all microbes.
- Povidone iodine may be prepared by any of a number of known routes, see, for example, European Published Applications No. EP-A-120301 and EP-A-6340, and British Patent No. GB-A-1580596.
- The amount of iodine incorporated in the iodophor used in the present cream will be determined by, amongst other factors, the amount of iodophor present in the cream and the required antibacterial strength of the cream. Preferably, iodine will constitute between 1 and 20% (by wt.), especially between 2 and 15% (by wt.) of the iodophor dry weight.
- The concentration of povidone iodine in the present cream will depend on the anti bacterial strength required. In addition, antibacterial agent concentration will be determined by, amongst other factors, the propensity of the agent to cause irritation, the length of use contemplated, the amount of iodine in the iodophor and the rate of iodine loss (when the cream is in use).
- The cream preferably contains enough iodophor to afford a concentration of available (titratable) iodine within the cream of between 0.1 and 2% (by wt.), especially between 0.2 and 1.5% (by wt.).
- Thus, a cream employing povidone iodine, with 10% (by wt.) available iodine, as an antibacterial agent, would preferably contain between 1 and 20%, especially 2 and 15% (by wt.) of povidone iodine.
- The topical cream base of the present invention is an oil in water emulsion and must contain between 20 and 50 per cent (by wt.) of a mixture of hydrocarbon and polyol moisturising components. Preferably the cream base contains between 25 and 40 per cent (by wt.) of hydrocarbon/moisturising components.
- The at least one hydrocarbon component of the present, cream base may be selected from any of the hydrocarbon oils and hydrocarbon bases that are well known in the pharmaceutical art. Suitable the hydrocarbon oils are mineral oil or liquid petrolatum, whilst suitable hydrocarbon bases are white petrolatum or white ointment (petrolatum with 5% beeswax).
- In a preferred embodiment of the present invention, the at least one hydrocarbon components comprises between 15 and 40% (w/w), especially between 20-30% (w/w) of the topical cream base.
- In a particularly preferred embodiment of the present invention, the at least one hydrocarbon component comprises a mixture of liquid petrolatum and white petrolatum.
- The at least one polyol moisturising component of the present cream base may be selected from any of the polyol moisturising components that are well known in the pharmaceutical art.
- Examples include propylene glycol and, which is preferred, glycerin.
- In a preferred embodiment of the present invention, the at least one polyol moisturising component comprises between 5 and 20% (w/w), especially between 5 and 15% (w/w) of the topical cream base.
- Although any ratio of hydrocarbon to polyol components that produces a satisfactory cream for topical application may be employed in the present cream base, the present inventor has found that ratios (w/w) between 1 to 1 and 4 to 1, especially a weight ratio of about 2 to 1, provide the most satisfactory cream bases for incorporation in the present topical cream.
- In addition to hydrocarbon and polyol moisturising components, the present cream base will generally also contain at least one emulsifier, and, optionally but preferably, at least one surfactant.
- Suitable emulsifiers include higher fatty alcohols, such as cetyl alcohol, stearyl alcohol, and cetostearyl alcohol, and partially esterified polyols such as glyceryl monostearate, polyethylene glycol monostearate and sorbitan monooleate.
- Preferably emulsifiers are provided at a concentration between 1 and 15% (by wt.) of the cream base.
- The present antibacterial cream must be of a viscosity that allows its topical application to the human or animal body. Preferably the cream will have a viscosity, at 25°C between 25,000 and 67,000 centipoises, when measured on a Brookfield (Trade Mark) LV Viscometer preferably between 30000 and 50000 centipoises.
- In order to facilitate the preparation of the present cream there is provided a process for the preparation of a topical, antibacterial cream comprising forming a mixture of an effective quantity of povidone iodine and a topical cream base, wherein the base comprises 20 to 50% (w/w) of a mixture of at least one hydrocarbon component and at least one polyol moisturising component. In one embodiment of the present process, the cream is prepared by forming an aqueous solution containing at least one antibacterial agent and at least one polyol moisturising component and then mixing this aqueous solution with the at least one hydrocarbon component. In another, preferred, embodiment of the present process, the cream is prepared by forming an aqueous solution of at least one polyol moisturising component, mixing the aqueous polyol solution with at least one hydrocarbon component to form a base and adding an aqueous solution of the antibacterial agent to the base. In either case, further components, e.g. emulsifiers, may be dissolved in either the aqueous or the hydrocarbon phase, as desired.
- In order to treat, for example, burns and other skin disorders, the present cream may be administered to the human or animal body by any of the conventional methods known in the medical/pharmaceutical art. For example, the cream may first be applied to a suitable dressing, such as a Teflon dressing, which is then placed on the wound tissue. The dressing may be held in place by a bondage. Generally, the dressing will be replaced every 12 to 24 hours. The cream may be applied alone or, although this is not necessary for successful treatment, in combination with a known acid cream, for example a benzoic acid containing cream, such as Aserbine (Trade Mark).
- Clinical trials using a povidone iodine cream according to the present invention have shown that the cream affords an improved penetration of the povidone iodine into wounds and that the cream has a superior therapeutic profile, when compared with PVPI products (especially ointments) of the prior art which contain a low content of hydrocarbon and moisturising components. In particular, the present cream has an improved (i.e. shorter) recovery than these prior art products and does not require the use of a desloughing agent, as do the prior art products.
- The present topical, antibacterial cream will now be described by way of example only.
- A topical antibacterial cream having the following ingredients
was prepared as follows:
The stearyl alcohol, cetyl alcohol, white petrolatum, liquid petrolatum, sorbitan monostearate and polyoxyethylene stearate were melted with mixing. Separately, PVPI was dissolved in water, after which the pH of the solution was adjusted to about 4.5 using NaOH. - An aqueous solution of polysorbate 60 and glycerine was then heated and added to the melt, with stirring, to form an emulsion. To the emulsion was added the PVPI solution, the whole being stirred until the batch reached room temperature. (During the final stage, water and/or hydroxide base may be added to the batch, as required).
- The resulting cream had a viscosity of 40000 centipoise at 25°C, measured on a Brookfield LV viscometer.
-
-
- (a) 10% Povidone iodine (Betadine, Trade Mark) ointment was obtained from Napp Laboratories, Cambridge.
- (b) 5% Povidone iodine cream was prepared as described in Example 1.
- (c) Aserbine (Trade Mark) cream containing benzoic acid (0.025%), malic acid (0.375%), salicylic acid (0.006%), propylene glycol and hexachlorophane, was obtained from Bencard, UK.
- Three groups, each consisting of 25 patients, were treated by topical application, on a once daily basis, of
- (i) 10% Betadine ointment mixed in equal proportions with Aserbine cream, or
- (ii) 5% Povidone iodine cream, or
- (iii) 5% Povidone iodine cream mixed in equal proportions with Aserbine cream.
- The daily application of fresh topical agent was preceded by wound cleansing in a whirlpool tank. Control of bacterial proliferation in the water and pump was achieved by adding PVPI to the water in a concentration of 3ppm. (This concentration has been shown to be effective in preventing bacterial proliferation and cross-contamination in hydrotherapy equipment).
- Systemic antibiotics were not employed except in those patients manifesting with signs and symptoms of invasive infection.
- The groups were comparable for age, size, type, depth and distribution of burn.
- All three preparations were applied easily and removed easily causing only mild discomfort on application in the majority of cases. Moderate discomfort on application was experienced by a few patients but was never severe enough to necessitate the use of analgesic agents. In no instance was it necessary to discontinue treatment because of discomfort. Results are shown in the Tables.
-
-
-
- Differences were observed in healing times. Superficial burns of between 20 and 30% total body surface area healed within 20-25 days when treated with PVPI cream with or without Aserbine, as opposed to an average of 36.5 days when treated with PVPI ointment plus Aserbine. Similar improved healing times were also seen in deep burns treated with the cream as opposed to those treated with the ointment plus Aserbine. Deep burns of between 40 and 50% total body surface area treated with the cream healed significantly faster than those burns of 20 to 30% total body surface area treated with the ointment plus Aserbine.
- In all of the above cases, it is important to note that the present cream which contains half as much PVPI as the ointment had significantly faster healing times.
- A decrease in positive bacterial cultures was observed for S.aureus and P.aeruqinosa in burns treated with PVPI cream with or without Aserbine as opposed to those treated with the ointment plus Aserbine.
- Apart from two patients who developed septicaemia which responded to systemic administration of tobramycin no other serious complications were observed.
-
- i) PVPI Ointment (Betadine, trade mark, ointment) available from Napp Laboratories, Cambridge.
- ii) PVPI Cream, prepared in accordance with Example 2 above.
- Trypticase Soy Bean Casein
Digest Broth (TSB) and Agar (TSA) - Staphylococcus Aereus ATCC 6538
- A stock culture of the test organism was maintained on TSA slants and was transferred to TSB 24 hours prior to the test. 0.2 ml. of the TSB culture was added to 5g. of each agent. After mixing, a 4mm loopful of the mixture was removed at intervals and was transferred to 10 ml. of TSB. Following incubation for 48 hr. at 33◊C, all cultures were examined for growth. Organism viability and carry over controls were carried out and were positive for growth for each agent.
- Two of the above tests were carried out. Results are shown in the Tables.
-
-
Claims (8)
- A topical, antibacterial cream comprising an effective amount of povidone iodine distributed in a topical cream base characterised in that the topical cream base is an oil-in-water emulsion containing water and 20%t to 50% (w/w) of a mixture of at least one hydrocarbon component and at least one polyol moisturising component.
- A cream according to claim 1 characterised in that the base comprises 25% to 40% (w/w) of a mixture of at least one hydrocarbon component and at least one polyol moisturising component.
- A cream according to either claim 1 or claim 2 characterised in that the at least one hydrocarbon component comprises mineral oil, liquid petrolatum, white petrolatum or white ointment, preferably a mixture of liquid petrolatum and white petrolatum.
- A cream according to anyone of claims 1 to 3 characterised in that the at least one hydrocarbon component comprises 15% to 40% (w/w), preferably 20% to 30% (w/w) of the topical cream base.
- A cream according to any one of claims 1 to 4 characterised in that the at least one polyol moisturising component comprises glycerin.
- A cream according to any one of claims 1 to 5 characterised in that the at least one polyol moisturising component comprises 5% to 20% (w/w), preferably 5% to 15% (w/w) of the topical cream base.
- A cream according to any one of claims 1 to 6 characterised in that the weight ratio of the at least one hydrocarbon component to the at least one polyol moisturising component in the topical cream base is between 1 to 1 and 4 to 1 and is preferably about 2 to 1.
- A cream according to any one of claims 1 to 7 characterised in that the topical cream base further comprises at least one emulsifier, preferably 1% to 15% (w/w) of at least one emulsifier.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ZA849673 | 1984-12-12 | ||
ZA849673 | 1984-12-12 | ||
CN198585109101A CN85109101A (en) | 1984-12-12 | 1985-12-12 | The preparation method of antibacterial ointment |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0185490A2 EP0185490A2 (en) | 1986-06-25 |
EP0185490A3 EP0185490A3 (en) | 1987-07-15 |
EP0185490B1 true EP0185490B1 (en) | 1991-09-25 |
Family
ID=36698676
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP85308814A Expired - Lifetime EP0185490B1 (en) | 1984-12-12 | 1985-12-04 | Antibacterial cream |
Country Status (18)
Country | Link |
---|---|
US (1) | US4671957A (en) |
EP (1) | EP0185490B1 (en) |
JP (1) | JPH0699298B2 (en) |
KR (1) | KR890001881B1 (en) |
CN (1) | CN85109101A (en) |
AT (1) | ATE67668T1 (en) |
AU (1) | AU576278B2 (en) |
CA (1) | CA1260833A (en) |
DE (1) | DE3584236D1 (en) |
DK (1) | DK170630B1 (en) |
ES (1) | ES8706437A1 (en) |
FI (1) | FI91935C (en) |
GR (1) | GR852972B (en) |
IE (1) | IE59827B1 (en) |
IL (1) | IL77224A (en) |
NO (1) | NO171095C (en) |
NZ (1) | NZ214496A (en) |
PT (1) | PT81618B (en) |
Families Citing this family (38)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3711083A1 (en) * | 1987-04-02 | 1988-10-13 | Euro Celtique Sa | PHARMACEUTICAL PREPARATION |
US4867967A (en) * | 1987-06-04 | 1989-09-19 | Crutcher Wilbert L | Method for the treatment of pseudofolliculitis barbae |
US5622708A (en) * | 1988-09-21 | 1997-04-22 | Ecolab Inc. | Erodible sanitizing caulk |
US5332577A (en) * | 1988-12-27 | 1994-07-26 | Dermamed | Transdermal administration to humans and animals |
US5241925A (en) * | 1988-12-27 | 1993-09-07 | Dermamed | Apparatus and techniques for administering veterinary medicaments |
IE63315B1 (en) * | 1989-04-24 | 1995-04-05 | Becton Dickinson Co | Radiation sterilizable antimicrobial ointment and process to manufacture |
US5324521A (en) * | 1989-12-18 | 1994-06-28 | Dermamed | Systems for transdermal administration of medicaments |
US5370876A (en) * | 1993-01-08 | 1994-12-06 | Microbarriers | Antimicrobial protective skin composition and method for protecting skin from body fluids |
US5512278A (en) * | 1994-01-11 | 1996-04-30 | Phylomed Corporation | Ointment base useful for pharmaceutical preparations |
US6623744B2 (en) * | 1995-06-22 | 2003-09-23 | 3M Innovative Properties Company | Stable hydroalcoholic compositions |
US7566460B2 (en) * | 1995-06-22 | 2009-07-28 | 3M Innovative Properties Company | Stable hydroalcoholic compositions |
EP1407761A1 (en) * | 1995-06-22 | 2004-04-14 | Minnesota Mining And Manufacturing Company | Stable hydroalcoholic compositions |
EP0833605A1 (en) | 1995-06-22 | 1998-04-08 | Minnesota Mining And Manufacturing Company | Stable hydroalcoholic compositions |
CA2265774C (en) | 1996-06-24 | 2009-05-05 | Bio-Safe Enterprises, Inc. | Antibacterial composition |
US6019997A (en) * | 1997-01-09 | 2000-02-01 | Minnesota Mining And Manufacturing | Hydroalcoholic compositions for transdermal penetration of pharmaceutical agents |
US6582711B1 (en) * | 1997-01-09 | 2003-06-24 | 3M Innovative Properties Company | Hydroalcoholic compositions thickened using polymers |
US5908619A (en) * | 1997-01-09 | 1999-06-01 | Minnesota Mining And Manufacturing Company | Hydroalcoholic compositions thickened using surfactant/polymer complexes |
US6582683B2 (en) | 2000-01-04 | 2003-06-24 | Skinvisible Pharmaceuticals, Inc. | Dermal barrier composition |
US20030017181A1 (en) * | 2001-05-31 | 2003-01-23 | Rood Gloria A. | Dermatological compositions and methods |
US6756059B2 (en) | 2001-08-20 | 2004-06-29 | Skinvisible Pharmaceuticals, Inc. | Topical composition, topical composition precursor, and methods for manufacturing and using |
JP4450406B2 (en) * | 2002-01-16 | 2010-04-14 | 学校法人日本大学 | A topical skin preparation containing Benicami kirifras as an active ingredient |
US20040101507A1 (en) * | 2002-11-27 | 2004-05-27 | Janco Predovan | Skin cream |
US20040126339A1 (en) * | 2002-12-31 | 2004-07-01 | Roszell James A. | Sunscreen composition and methods for manufacturing and using a sunscreen composition |
EP1872788B1 (en) | 2005-04-08 | 2013-05-22 | Mie University | External agent for treating wounds |
DE102005045145A1 (en) * | 2005-09-15 | 2007-03-29 | Schülke & Mayr GmbH | Use of octenidine dihydrochloride in semisolid preparations |
US20100137333A1 (en) * | 2006-10-20 | 2010-06-03 | Roszell James A | Antifungal composition and methods for using |
US8128913B1 (en) | 2007-12-06 | 2012-03-06 | Skinvisible Pharmaceuticals, Inc. | Sunscreen composition with enhanced UV-A absorber stability and methods |
US8299122B2 (en) * | 2008-04-14 | 2012-10-30 | Skinvisible Pharmaceuticals, Inc. | Method for stabilizing retinoic acid, retinoic acid containing composition, and method of using a retinoic acid containing composition |
DE102010004950A1 (en) * | 2010-01-18 | 2011-07-21 | Remis Gesellschaft für Entwicklung und Vertrieb von technischen Elementen mbH, 50829 | Cooling shelf with door device |
US20140348774A1 (en) * | 2010-12-10 | 2014-11-27 | Aurora Pharmaceutical, LLC | Method for treating wounds and tissue repair |
MX345458B (en) * | 2011-05-11 | 2017-02-01 | Veloce Biopharma Llc | Antifungal compositions for the treatment of skin and nails. |
TW201605444A (en) * | 2013-12-18 | 2016-02-16 | 阿爾米雷爾有限公司 | Topical pharmaceutical or cosmetic compositions comprising octenidine dihydrochloride |
SG11201701928RA (en) | 2014-09-12 | 2017-04-27 | Antibiotx Aps | Antibacterial use of halogenated salicylanilides |
GB201509326D0 (en) | 2015-05-29 | 2015-07-15 | Antibio Tx Aps | Novel use |
EP3310334A1 (en) | 2015-06-22 | 2018-04-25 | Infection Containment Company, LLC | Topical antiseptic system |
KR102564048B1 (en) * | 2015-09-30 | 2023-08-04 | (주)아모레퍼시픽 | Oil-in-water type emulsion composition |
US11419834B2 (en) | 2019-02-25 | 2022-08-23 | Rhode Island Hospital | Methods for treating diseases or infections caused by or associated with H. pylori using a halogenated salicylanilide |
CA3074150A1 (en) | 2020-02-18 | 2021-08-18 | Ovation Science, Inc. | Composition and method for transdermal delivery of cannabidiol (cbd) and delta9-tetrahydrocannabinol (thc) |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4017641A (en) * | 1975-01-31 | 1977-04-12 | The Procter & Gamble Company | Skin moisturizing compositions containing 2-pyrrolidinone |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4049802A (en) * | 1975-03-19 | 1977-09-20 | Research Corporation | Zinc sulfadiazine and its use in the treatment of burns |
DE2851544C2 (en) * | 1978-11-29 | 1985-09-26 | Beiersdorf Ag, 2000 Hamburg | Fluocortolone cream |
US4271149A (en) * | 1979-09-21 | 1981-06-02 | West Agro-Chemical, Inc. | Germicidal iodine compositions with enhanced iodine stability |
US4301145A (en) * | 1980-07-28 | 1981-11-17 | Cestari Joseph E | Antiseptic skin cream |
EP0103911A1 (en) * | 1982-06-30 | 1984-03-28 | THE PROCTER & GAMBLE COMPANY | Emollient-containing topical pharmaceutical compositions |
GR77517B (en) * | 1982-06-30 | 1984-09-24 | Procter & Gamble |
-
1985
- 1985-12-04 IL IL8577224A patent/IL77224A/en not_active IP Right Cessation
- 1985-12-04 DE DE8585308814T patent/DE3584236D1/en not_active Expired - Lifetime
- 1985-12-04 AT AT85308814T patent/ATE67668T1/en not_active IP Right Cessation
- 1985-12-04 EP EP85308814A patent/EP0185490B1/en not_active Expired - Lifetime
- 1985-12-05 PT PT81618A patent/PT81618B/en unknown
- 1985-12-06 AU AU50859/85A patent/AU576278B2/en not_active Expired
- 1985-12-09 US US06/806,763 patent/US4671957A/en not_active Expired - Lifetime
- 1985-12-09 NO NO85854943A patent/NO171095C/en not_active IP Right Cessation
- 1985-12-10 CA CA000497275A patent/CA1260833A/en not_active Expired
- 1985-12-10 NZ NZ214496A patent/NZ214496A/en unknown
- 1985-12-11 GR GR852972A patent/GR852972B/el not_active IP Right Cessation
- 1985-12-11 DK DK574185A patent/DK170630B1/en not_active IP Right Cessation
- 1985-12-11 KR KR1019850009330A patent/KR890001881B1/en not_active IP Right Cessation
- 1985-12-11 ES ES549814A patent/ES8706437A1/en not_active Expired
- 1985-12-11 IE IE312685A patent/IE59827B1/en not_active IP Right Cessation
- 1985-12-11 JP JP60278845A patent/JPH0699298B2/en not_active Expired - Fee Related
- 1985-12-11 FI FI854886A patent/FI91935C/en not_active IP Right Cessation
- 1985-12-12 CN CN198585109101A patent/CN85109101A/en active Pending
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4017641A (en) * | 1975-01-31 | 1977-04-12 | The Procter & Gamble Company | Skin moisturizing compositions containing 2-pyrrolidinone |
Also Published As
Publication number | Publication date |
---|---|
ES549814A0 (en) | 1987-07-01 |
ES8706437A1 (en) | 1987-07-01 |
IE853126L (en) | 1986-06-12 |
US4671957A (en) | 1987-06-09 |
NO854943L (en) | 1986-06-13 |
PT81618A (en) | 1986-01-01 |
IL77224A (en) | 1989-09-10 |
CN85109101A (en) | 1987-06-24 |
EP0185490A2 (en) | 1986-06-25 |
DE3584236D1 (en) | 1991-10-31 |
IE59827B1 (en) | 1994-04-06 |
PT81618B (en) | 1987-10-20 |
FI854886A0 (en) | 1985-12-11 |
DK170630B1 (en) | 1995-11-20 |
DK574185A (en) | 1986-06-13 |
NO171095B (en) | 1992-10-19 |
ATE67668T1 (en) | 1991-10-15 |
NZ214496A (en) | 1989-03-29 |
JPS61186312A (en) | 1986-08-20 |
JPH0699298B2 (en) | 1994-12-07 |
NO171095C (en) | 1993-01-27 |
FI91935C (en) | 1994-09-12 |
GR852972B (en) | 1986-04-01 |
EP0185490A3 (en) | 1987-07-15 |
DK574185D0 (en) | 1985-12-11 |
AU576278B2 (en) | 1988-08-18 |
CA1260833A (en) | 1989-09-26 |
KR890001881B1 (en) | 1989-05-29 |
FI91935B (en) | 1994-05-31 |
AU5085985A (en) | 1986-06-19 |
FI854886A (en) | 1986-06-13 |
KR870005638A (en) | 1987-07-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0185490B1 (en) | Antibacterial cream | |
RU2032402C1 (en) | Composition and method for treating vaginitis | |
EP0715852B1 (en) | Use of hyaluronic acid or its salt to treat skin disease | |
US6645510B1 (en) | Method of treating topical ailments | |
EP0112852A1 (en) | Pharmaceutical gel composition. | |
US5137718A (en) | Infection fighting composition for topical application | |
US4124720A (en) | Therapeutic hydrodispersible emulsion | |
CH653892A5 (en) | Wound medication for covering wounds and burns. | |
US20030104018A1 (en) | Skin product having micro-spheres, and processes for the production thereof | |
CA2535004C (en) | Topical veterinary compositions and methods for the treatment and prevention of infection | |
RU2291694C2 (en) | Pharmaceutical composition containing fungicide, bacteriostatic sulfonamide and antibacterial substance for topical using | |
CN113056257A (en) | Semisolid oil-based pharmaceutical composition containing pirfenidone for tissue repair | |
EP1069898B1 (en) | Topical antiseptic compositions and methods | |
US4600711A (en) | Composition for topical and infusion treatment of wounds and burns | |
Stewart et al. | The treatment of patients with interstitial cystitis, with special reference to intravesical DMSO | |
US4717737A (en) | Anti-bacterial methods and agent | |
WO2003041723A1 (en) | Pharmaceutical applications of hyaluronic acid preparations | |
RU2202362C2 (en) | Composition for topical usage containing human epidermis factor growth | |
US4752617A (en) | Anti-bacterial methods and agents | |
KR0145678B1 (en) | A podophyllotoxin preparation containing triglycerides | |
JPH11512417A (en) | Antiseptic skin care composition and preparation method thereof | |
US9345720B2 (en) | Composition and method for treating wounds | |
De Kock et al. | A study to assess the effects of a new Betadine cream formulation compared to a standard topical treatment regimen for burns | |
US4590212A (en) | Method of increasing the rate of wound healing and composition | |
RU2175549C1 (en) | Wound-healing medicinal preparation "zooderm" |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Kind code of ref document: A2 Designated state(s): AT BE CH DE FR GB IT LI LU NL SE |
|
17P | Request for examination filed |
Effective date: 19861022 |
|
PUAL | Search report despatched |
Free format text: ORIGINAL CODE: 0009013 |
|
AK | Designated contracting states |
Kind code of ref document: A3 Designated state(s): AT BE CH DE FR GB IT LI LU NL SE |
|
17Q | First examination report despatched |
Effective date: 19890104 |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): AT BE CH DE FR GB IT LI LU NL SE |
|
REF | Corresponds to: |
Ref document number: 67668 Country of ref document: AT Date of ref document: 19911015 Kind code of ref document: T |
|
ITF | It: translation for a ep patent filed |
Owner name: BUGNION S.P.A. |
|
ET | Fr: translation filed | ||
REF | Corresponds to: |
Ref document number: 3584236 Country of ref document: DE Date of ref document: 19911031 |
|
PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
26N | No opposition filed | ||
REG | Reference to a national code |
Ref country code: GB Ref legal event code: 732E |
|
EPTA | Lu: last paid annual fee | ||
EAL | Se: european patent in force in sweden |
Ref document number: 85308814.4 |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: IF02 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: AT Payment date: 20041109 Year of fee payment: 20 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 20041111 Year of fee payment: 20 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 20041115 Year of fee payment: 20 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: LU Payment date: 20041116 Year of fee payment: 20 Ref country code: GB Payment date: 20041116 Year of fee payment: 20 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 20041117 Year of fee payment: 20 Ref country code: CH Payment date: 20041117 Year of fee payment: 20 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: SE Payment date: 20041118 Year of fee payment: 20 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: BE Payment date: 20041201 Year of fee payment: 20 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GB Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION Effective date: 20051203 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION Effective date: 20051204 |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: PE20 |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
NLV7 | Nl: ceased due to reaching the maximum lifetime of a patent |
Effective date: 20051204 |
|
EUG | Se: european patent has lapsed | ||
BE20 | Be: patent expired |
Owner name: S.A. *EUROCELTIQUE Effective date: 20051204 |